Gossip Girl: Generation NeXt
by bookworm7117
Summary: Henry Charles Bass: Playboy, troublemaker. Heir to the throne of St. Jude's. Every girl loves herself a bad boy, but we're wondering if little Hen can keep up. Straight "A"s? Wonder whose pants you had to get into that make that happen? Unless our Dark Prince in the making isn't all his reputation has him cracked up to be? Stay tuned. XOXO Gossip Girl
1. Apples

Gossip Girl: Generation NeXt

AN: I've added new characters as well as old ones. Some names (especially last names) should look familiar. It's no coincidence GG is doing Character Profiles...I want you all to know who the newbies are. That being said, if you have any questions about who a character is or who's related to who, just leave me a review and I'll be sure to message you back! (: Happy Reading.

Chapter 1: Apples

**Welcome back to reality, Upper-East-Siders. Hope summer in the Hamptons didn't make you forget about me. Get out those designer pencil pouches because school's back in session in less than a week. Good news, too, because I was getting the summer blues. It's always more fun when our favorite trust-fund babies are all back in the same playground. Our beloved fresh-meat moving up the food-chain…One would hope that would mean growing up as well, but where's the fun in that? With a new school year, comes new readers. Gotta initiate the freshmen. With that being said, I'll be doing character profiles. Don't worry, no mug-shots involved…****_yet_****! Here's me, crossing my fingers. XOXO Gossip Girl**

_Great. _Henry sighed. _Character profiles could only mean one thing: total humiliation. _**  
**

"Mom, Dad, I'm home," Henry called as the elevator chimed to let him enter his townhouse.

"Do you really have to do that every time?" his best friend, Theo, asked skeptically.

"If I want to refrain from seeing my parents fornicating on the furniture then yes," Henry rolled his eyes as Theo shivered in disgust.

The two boys made their way to the kitchen, where they knew the bar would always be stocked full of scotch.

"You know, that's probably the best thing about having screwed up parents who aren't even together anymore…they are _never_ home. And they never…_you know_."

Just as the boys rounded the corner, they shouted out with shock and disgust.

"Oh my god!" Henry shielded his eyes from the scene before him, turning away immediately.

Theo's eyes grew huge as his face grew red. He dropped his gaze to the floor and brought his hands up to his forehead to block out any further images pervading his mind.

"Seriously Mr. and Mrs. B, you know it's bad when even your son's best friend catches you two getting it on in the kitchen…Several times."

Blair and Chuck were embarrassed, but not nearly as embarrassed as they should have been. Blair had been pinned on the kitchen counter, bra discarded, and skirt pulled up to her waist. Chuck's tie was nowhere to be found and his shirt was completely unbuttoned. His pants were getting there, but thankfully the two boys had not arrived a few minutes later. They would have caught the full-on act. When Henry and Theo walked in, Chuck had one breast in his mouth, the other in his hand. Blair's fingers were clawing at Chuck's scalp, and her legs were wrapped tightly around him.

It was sad to say that Henry had seen much worse from his parents.

Chuck covered Blair up with his own shirt, and then she retrieved her discarded clothing and straightened out her skirt.

Blair laughed nervously a bit at Theo's comment, "Oh come on, Theo you're being dramatic. It can't have been _that _many times."

Theo glanced up to give her a sarcastic look, but he immediately regretted it seeing the Basses still scantily clad. His eyes quickly shot back to the floor as he mumbled, "Oh it's been at least four times now."

Blair waltzed around the corner to the bathroom to straighten out her wardrobe and fix her hair.

"Honestly, it's gotten so bad I'm afraid to have people over," Henry growled.

"You should be happy for us…for keeping our marriage alive," Chuck retorted, smirking.

"Yes, good for you," Henry sneered. "But can't you 'keep your marriage alive' in say your master bedroom?"

"Where's the fun in that?" Chuck smirked.

Blair finally returned in a presentable condition. She tossed Chuck's shirt back at him.

"You know, other people don't have to worry about their parents having sex all the time. Let alone in unusual places."

"You're a Bass, Henry. You're not other people," she rolled her eyes.

"Wish I was," he mumbled.

"What was that, dear?" Blair shot him an icy look.

"Nothing, mother," he growled under his breath. "And what about the party tonight in like an hour? Did you two just forget about that?"

"I only need 20 minutes."

"Really, Mr. Bass?" Theo grimaced.

Chuck was fully dressed again. Blair walked over to him, placing her hand on his chest as his arm wrapped around her. She gave him a kiss that started to deepen until she pulled away.

"You children can come out now," Blair giggled.

Henry rolled his eyes, pushing past his parents to the bar. Theo squirmed, looking up nervously and frantically. He sighed when he saw that everything was actually all clear.

"I need a drink," Henry muttered.

"I don't know where you get your aversion to PDA between your mother and I. Because we both…"

"Don't even say you both like to watch," Henry was mortified.

Blair laughed, smacking Chuck on the chest, "He's just as disgusted as Serena always is."

"Speaking of…not too much, Hen," Blair took on a more serious note as she gestured toward the scotch her son was already downing. "At least not before the party, you know how judgy your Aunt Serena and Uncle Dan can be."

"It's not like Ali hasn't been "_corrupted"_ by alcohol before," Theo snickered.

"All the same, we don't need another Blerena face-off," Chuck snickered as well. "Now if you two will excuse us, we have some unfinished business to attend to."

Chuck grabbed Blair and lifted her into his arms. She started giggling uncontrollably as he raced up the stairs toward their bedroom with her.

"Is it like that all the time?" Theo asked, sitting next to Henry at the bar.

He nodded, "I've seen more of my parents than I care to admit."

"At least their happy," Theo trailed off, looking a bit melancholy.

"I guess."

**Listen up Upper East Siders, word on the street is the Basses are throwing yet another "family" get together. Reminiscent of the annual Back to School Party, isn't it B? I guess we never do grow out of high school. Here's me hoping that Bass Jr. can cause half the trouble his parents did. XOXO Gossip Girl.**

An hour later, Henry was still at the bar, attempting to drink away the images his brain was scarred with. He checked Gossip Girl, and chuckled to himself. Everyone kept waiting to see what kind of Bass he would be. Was he the troubled, dark womanizing player like his father? Or the ambitious, manipulative ruler of the school like his mother? Henry had no idea.

"Dad sent me to tell you to quit drinking," Henry's annoying little sister, Delia, announced.

"Well you can tell _Dad_—"

She held up a hand, "Please, I don't do messenger girl."

He rolled his eyes. His sister was a total pain in his ass. She was bossy, sarcastic, proud, arrogant, spoiled, and snobby. Not to mention, she had a knack for getting herself into and out of sticky situations. She loved danger and trouble, but she hated getting caught.

Henry ran his palm across his face, "Fine, whatever. Just leave me alone."

"Gladly," Delia turned to spin away. "Do you know where J.J. is by chance?"

Henry rolled his eyes. J.J. was their cousin of sorts. Their Great Uncle Jack had married Georgina Sparks, who had given birth to the devil spawn of this world—James Jackson Bass; J.J. for short. He was a sixth grader like Delia, and the two of them had been fast friends. Henry knew his mother despised the friendship, but J.J. was family. And if Henry Bass had learned anything in his sixteen years on the Upper East Side of Manhattan, it was that family, especially _his_ family, was unavoidable.

"Probably off torturing kittens or something of that nature," Henry slid off his seat, in search of some real company.

Delia rolled her eyes, and sped off to find her partner in crime. From a young age, Henry had realized how screwed up his family truly was. There were too many step-siblings and ex-step-siblings to keep track of.

"Henry, look how grown up you are," his Aunt Serena smiled, hugging him. He loved his aunt. She was his mother's best friend, and his father's step-sister. Her mom, Lilly, had adopted his father after his grandpa faked his death…it was a long story. Aunt Serena was bubbly, happy, and charming. He appreciated the fun, light-hearted times he had with her.

"You look just like your father did at that age," she grinned at her husband, Dan. "Doesn't he?"

Uncle Dan quirked an eyebrow, "Absolutely. It's actually kind of terrifying."

Henry laughed with his aunt and uncle, but inwardly he was rolling his eyes. He had heard that his whole life. He was a mini Chuck Bass. It haunted him. People expected him to be a bad boy: a womanizing, partier, who got high and wasted all the time. His father really had quite the reputation as a teenager. It just added to Henry's identity crisis.

"And I see the apple doesn't fall far from the tree," Dan added, noticing the stench of scotch Henry carried with him.

Henry grinned, "You caught me, Uncle Dan."

He really wanted to hear this next lecture. Uncle Dan was amusing in the sense that you could tell he just simply wasn't born into the Upper East Side. He had convinced Aunt Serena that alcohol had ruined her life, so they had decided to be strict about drugs, alcohol, and partying with their children. Of course, this led to intense arguments between his parents and his aunt and uncle. Usually it was mostly just his mom and Aunt Serena disagreeing. Then his mom would say something bad about Uncle Dan. He knew his dad pretty much despised the guy, and his mom wasn't really a fan either.

The weirdest thing was that his mom had dated his Uncle Dan. His parents were always open and honest with him…almost a bit too open, actually. They'd told him all about their past because it was sort of common knowledge. If he ever really wanted to know something, he could pretty much just look it up on the original Gossip Girl blog.

So basically he knew his mom had had sex with his Uncle Dan at one point. She'd also had sex with "Uncle" Nate and Great Uncle Jack. She had dated "Uncle" Nate in high school. His father had pretty much slept with the whole Upper East Side including his Aunt Jenny, but thankfully not his Aunt Serena.

Uncle Dan sighed, "Look, Henry, I know I'm not your father, and I know your parents are probably okay with it, but I just hope you know what you are doing. Alcohol can ruin your life, and I'd just hate to see that happen to someone with as much potential as you."

Henry smiled his fakest smile, "Well Uncle Dan, thanks for your concern, but seeing as my parents are the most successful and powerful people in Manhattan, and they've never been strangers to alcohol, somehow I'm inclined to believe everything will turn out alright."

"Your parents are the exceptions, not the rule, Henry. It's only because they found each other that they—"

"Alright, that's enough, Dan," Serena smiled at him, grabbing his arm. "I don't want another fight with Blair over this."

Dan sighed, giving up. Henry was used to hearing all about his parents' great love. Their whole journey to be together. It just sounded complicated to him. He had to admit that he had seen this great love in action, and he wanted something like it. He wanted to look at someone the way his father looked at his mom. He wanted to love someone the way they loved each other because now that he had seen the real thing, he knew he could never settle for less. What Uncle Dan and Aunt Serena had was less.

"Excuse me," Henry smiled at his aunt and uncle, dropping the act the second he turned his back.

...

AN: Hope you all enjoyed the first chapter. Again, any questions, comments, constructive criticism? Leave it all in the reviews please and thank you(:


	2. Bea Aggressive

Chapter 2: Bea Aggressive

**First up on our Character Profile list, more like Character Torture, is none other than Theodore William Archibald. Oh wait, T, I forgot…you prefer going by Richardson. Soon you'll learn in the UES, last name is everything. Better fix up those daddy issues if you want to get anywhere, Theo. Back to business…T son of Gossip Girl legend, Nathaniel Archibald, our beloved Golden Boy sure seems to shine almost as bright. Of course, if he follows in his father's footsteps, then watch out ladies, Theo just might be the next manwhore. I don't know about the rest of you, but I'm sure hoping little Archibald's moral compass is a bit more skewed than his father's ever was. That shouldn't be too hard, considering his daddy didn't even ****_want_**** him for two years. How's it feel, T? You're best friend, Henry, sure wouldn't know. XOXO Gossip Girl.**

Henry easily spotted Theo across the room. His best friend was popping his knuckles, the telltale sign that he was nervous. It was then that Henry realized who he was conversing with.

"Uncle Nate," Henry nodded.

"Henry!" Nate hugged his favorite "nephew." They weren't actually related, but Nate was his dad's best friend, so he was family.

"Feels like I haven't seen you in ages."

"Well you've been pretty busy, Senator," Henry teased.

"How are things going with school and everything? Got yourself a girl yet?"

"School's school. Mom and Dad can pretty much bail me out of anything. Money talks, you know. As far as girls go…let's just say I'm keeping my options open."

Nate snorted, "I'm sure you are."

Theo jumped in, "Please, Bea is all over you. You know that's happening this year."

Theo loved teasing Henry about Bea. It actually _wasn't _happening. Beatrice and Henry were great friends. They were total opposites and their parents had totally opposite expectations of them. One of Theo's favorite pastimes was playing matchmaker, or at least joking about it. Bea and Henry were the perfect joke because Henry was a total playboy and Bea had never been kissed.

"Bea?" Nate smirked.

"She's the current Queen Bea of Constance. A bit too tightly wound for my taste," Henry blew it off.

"That's right. You prefer loose women," Theo retorted.

"They get the job done. The blow-job, I mean," Henry smirked.

Nate rolled his eyes, "Some day you'll realize all your missing out on."

"Buying flowers, talking about feelings, making compromises…" Theo snickered. "We sure are miserable without it all."

Nate just grinned, shaking his head, "See you around, Hen. I'm gonna go find your dad, tell him how _proud_ he should be."

Henry wasn't sure if Nate was being serious or not. It seemed like a joke, but honestly, his dad probably _would _be proud of his behavior. That's why Henry tried to be the playboy. It was the reputation his father always had, and it was what everyone expected from him since he was old enough to understand the difference between a girl and a boy.

Nate turned to Theo before leaving and took on a bit more of a serious note, "I hope you'll consider what we discussed."

Theo just nodded, loosing his smile.

"What was that all about?" Henry wondered, after Uncle Nate was out of earshot.

"Nothing…"

"Come on, man. Don't disrespect my intellect, that was _something_."

"He wants me to move in with him."

"You're kidding."

Theo shook his head.

"But he lives in D.C. That's crazy."

Theo bit his lip.

"You told him that's crazy right?"

"He's actually moving back to Manhattan…"

"How can he? With his governmental duties and shit?"

"Apparently his withdrawing after his term is over…which happens to be this November. It was never his idea to run for office. His grandfather pushed him. He's never enjoyed the atmosphere. D.C. is overrun with corruption."

"Like the UES is any better…" Henry mumbled.

"He misses _The Spectator._ And…he wants to be closer to me."

"So he asked you to live with him?"

"He gave me the option. He said I could choose how often I wanted to stay at his place as opposed to my mother's. He said he wants to get to know his son, so his door is always open."

"So are you going to do it? Live with him?"

"I dunno..."

They boys stood there in the corner, leaning in the wall in silence. Theo cracked a smile, "We're talking about this like a bunch of girls. "Oh my god, he asked me to move in with him! It's such a big decision!"'

Henry guffawed in uncontrollable laughter. He barely managed to get out, "_Never_, and I mean _never, _use that creepy girl voice again. That's scary as shit."

Theo laughed at his best friend, rolling his eyes, "Like you haven't seen scarier shit...that trany in-"

Henry cut him off, "We agreed _never_ to speak of that-"

"I know, I know," Theo chuckled at his friend's automatic shift in demeanor. "Just messing with you, man."

The boys settled into an easy silence. Both of them had a lot on their minds.

"Sometimes I feel like you know my dad better than I do," Theo mused. "And sometimes I feel like he likes you better than me. Like you two actually have a connection. With me and him it's just…awkward."

"That's not true," Henry wasn't that great at the whole comforting thing, but he was trying. "He's just known me since I was born. He only found out about you two years ago."

"That's still so twisted. My great grandfather paid off my mother so my dad would never find out about me."

"Sounds like good old juicy UES drama."

"It took him a whole two years to decide he even wanted to know me, though. All of the sudden, he wants me to live with him. What changed?"

"I don't know. Maybe he just realized he was being a dick by ignoring you. Maybe he's now fully comprehended the idea that he has sixteen year old son that he never knew he had."

"I can't believe we were friends before we knew any of this."

"Life is full of crazy coincidences, I suppose."

"It's so trippy."

"I do hope you're referring to the LSD I snuck you the other day, young Theodore," Gregor grinned.

"You know I don't do hallucinogenics, _Greg_."

"Right, I forgot. You only do depressants because you're such _a bore_. What's kicking, Baby Bass? Got anything good on you?"

"Not at the moment, Gregor."

"Tsk, tsk. Don't go soft on me, Hen."

The best friends both admired and despised Gregor Van Der Bilt. They admired him because he had everyone fooled. They despised him because he had everyone fooled. He was the son of Nate's cousin, Trip. He was a charmer who could win over anyone's heart, but behind that carefully plotted heartthrob, golden boy façade, he was the devil. Obviously he had snuck into the party because he certainly was not invited.

"Wouldn't dream of it," Henry remarked sarcastically.

"So, fill me in on the new meat this year. Once they turn sixteen, they're fair game…Who are those chicks you two hang around all the time: Isabella, Beatrice…and what is it? Jo—something?"

"Jocelyn," Theo replied, annoyed.

"Jocelyn, right. So spill, Baby Bass."

"First of all, stop calling me Baby Bass. Second of all, you're a disgusting pig, and while I respect your methods and reputation, I have to hope that all three of our _friends _will have the self-respect to see through your Prince Charming disguise."

Gregor just chuckled, "So Hen-Hen here, has clearly been bitten by the love bug? But which unlucky girl has stolen the poor boy's heart away, Theo?"

"As if I'd tell you."

"Is it Isabella? The party girl? I bet she gets pretty _frisky_," he wagged his eyebrows at the two.

Henry and Theo were both growing more and more furious by the second. Gregor knew just how to push their buttons.

Gregor sighed at their silence, "Don't even pretend like you haven't tapped that ass, Bass."

Henry shifted a bit uncomfortably.

"Okay then it must be Jocelyn. JoJo the crazy girl. I bet she's into some pretty weird shit. Are her tits really as big as they look, Bass? I bet they wouldn't even fit into your tiny girl hands."

"That's enough, Gregor," Theo stepped in.

He laughed in his face, "Step down, little boy. The men are playing here."

Theo backed off, embarrassed. Gregor knew just where to hit him. Theo was slightly embarrassed at his lack of…experience with women. He was a virgin.

Henry was fuming. Sure, yes, he had thought about these girls sexually. Maybe he had even fucked them…a few times. But no one disrespected them like that. Especially not Gregor. He fooled everyone at school that he was some kind of honest Abe. A real gentleman, a prince charming, but Bass knew that deep down Gregor was worse than he was.

"Alright, bring out girl number three!" Gregor called in his announcer voice. "Beatrice!"

"Queen B of the school, uptight, prissy, a snobby little princess. With all that built up tension, I bet she just goes _pure animal_ when she unwinds. Bet you have the scratch marks to prove it, huh Bass?"

Henry growled, "That's enough, Gregor."

"Ding, ding, ding, we have a winner!"

Henry's fists clenched.

"Should I tell the lucky lady?" Gregor's eyes lit up with amusement. "Nah, I'll just wait. That can be saved for pillow talk."

"I'm gonna make her fall in love with me, Bass. She's gonna beg me for my big cock. She'll be purring my name in my ear as I fuck her senseless. She'll forget all about you. And when I'm done with her, she'll be _nothing_. I'll leave her worthless and wasted like a used tissue. Something you throw in the garbage and never look for again."

That was it. Henry punched Gregor as hard as he could right in the face. Gregor stumbled back, laughing like a fool. Then everyone turned around to see the commotion, and Gregor's acting face came out again. He held his jaw and looked at Henry pleadingly.

"Look, man, I'm sorry. I didn't—" he turned away, pretending to look hurt. "I shouldn't have come."

The whole room gasped and looked at Henry like he was the animal. They gave him icy glares. How could he punch Gregor Van Der Bilt? He was such a nice young man! The whispers were never-ending. And then of course, right on time:

**Uh, oh! Looks like Henry Bass is living up to his potential after all. Our beloved Prince Charming ran away from the ball, but instead of a glass slipper, he got a fist in his face. Wonder what has H so hot and bothered? Hope the bruise heals nicely. Wouldn't want to mess up that pretty face of yours, G. XOXO Gossip Girl.**

...

AN: Again, leave whatever comments, suggestions, questions, etc. you have in the REVIEWS! Promise to get back to you! I would LOVE to hear what you all think of this fic so far(:


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